The Journal of Organic Chemistry

Preparation of rearranged allylic isocyanates from the reaction of allylic alkoxides with cyanogen chloride

LE Overman, M Kakimoto

Index: Overman,L.E.; Kakimoto,M. Journal of Organic Chemistry, 1978 , vol. 43, p. 4564 - 4567

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Citation Number: 15

Abstract

As a potential room temperature method for allylicdy transposing hydroxyl and amino functions, the reaction of cyanogen chloride with the lithium salt of four representative allylic alcohols was examined. Such treatment results in the formation, in good yield, of a mixture of the allylically rearranged isocyanate and a dimeric carbamate. The allylic isocyanate 4 results from rapid [3, 3] sigmatropic rearrangement of the initially formed allylic cyanate 3, ...